Betting on professional basketball may be daunting for most, but these canny handicappers have made a living from shrewd insights in the NBA

Spend time around sharp sports bettors and you inevitably hear them gripe and brag over every competitive outcome you can imagine. Guys rail against the road conditions of NASCAR or Tiger performing better or worse than he should. Or they sing the glories of getting in gear with an obscure division of the NCAA or spotting a glitch in the NFL team that everybody else seems to think is infallible.

What you rarely hear, though, is chatter about the NBA. Serious sports bettors often go easy on their pro basketball betting. “It’s too hard to beat,” says a respected gambler. “Everything is totally fluid. It’s not like the NFL, where there’s only one game a week and you can read into what happens. Additionally, says Jay Rood, vice president of race and sports for MGM Resorts, “It’s hard to know the weight that coaches put on the schedule. How aggressive will they be against nonconference foes when there is a conference game coming up? With college you get a [more consistent] effort on an ongoing basis.”

But the NBA does not intimidate everyone. This becomes apparent when I wash up on the shores of E.R. Island—okay, the metaphorical shores. It’s actually the home of Erin Rynning, situated on a rustic stretch in the Las Vegas suburb of Summerlin, behind the security gates of a nice housing development. Rynning is famous for being the second most successful NBA sports bettor out there. Number one is a guy by the name of Bob Voulgaris but he’s holed up somewhere between Beverly Hills and Vancouver. Word comes from a mutual friend that Voulgaris is taking no calls from the media these days. He works from a strong computer system that models games and divines scores. He initially made a killing by beating the halftime lines put out by bookies. Once those inefficiencies got fixed, Voulgaris turned to hammering the full-game spreads and money lines and totals.

Nevertheless, for Rynning, being number-two ain’t so bad. Living on his theoretical island, sitting at a table in his tidy kitchen, laid-back and post-preppy looking, Rynning is as happy a guy as you’ll find splashing around money for a living. He’s understood NBA basketball for as long as he can remember, never needed to have a square job, and always knew that he would eventually end up in Las Vegas. In his Spartan, two-story home, which feels far from the pulsing Vegas Strip, Rynning maintains a low-tech operation. He does his handicapping with pen and paper, working mostly on gut and instinct rather than following the mandates of software.

It’s an old-fashioned way that has long worked like a charm. For him, he insists, beating the NBA has never been the big chore that it is for others. “I began handicapping right from the start, back when I was 12 years old,” says Rynning, who grew up in Wisconsin.

“During ninth grade, my father’s friends would call and ask me who to bet on. I’ve never met anyone with better opinions than me. That’s why I avoid the sports books”—where distracting conversations about lines and odds are inevitable—“and don’t discuss the games with other bettors. When I first moved here, 10 years ago, I thought it would be great to take in information from all the handicapping shows on the radio. I did, and 2003 was the only losing year I’ve ever had. Now I just stick with my own opinions and things work out fine.”

While others see a certain degree of opacity in the NBA games, Rynning likes the lack of short-term volatility. He enjoys the fact that a single play is unlikely to mark the difference between winning a bet and losing one. “In the NBA, we have 1,230 games,” says Rynning who sells a couple of picks per night via his website sportsmemo.com. “One basket is one percent of the total score. If somebody fails to block a three-pointer, it’s not the same thing as someone hitting a home run with bases loaded. That’s a single play, that could have been an out, and yet it can easily determine winning or losing a bet.”

In terms of doing the actual work that makes him into a superstar NBA bettor, Rynning says that he creates power ratings and comes up with total scores that each team should manage to put on the board. Then he tweaks numbers based on the particular matchup and looks for overlays. Beyond that, he says, “I’ve trained myself to think in a certain way. Whatever information I come across, I translate it into value.”

Figuratively speaking, he likes to get in the locker room and find edges in the chemistry that arise from the comings and goings of various players. In 2011, for instance, when Carmelo Anthony got traded from the Denver Nuggets to the New York Knicks, the betting lines reflected conventional wisdom that Denver would be hurt by Anthony’s departure. “He had chemistry problems with Denver and was holding the team hostage over his negotiations,” says Rynning. “Unlike everybody else, I thought Denver would be better without him. I was right. I made a lot of money in betting against Carmelo Anthony.”

He’s also made a lot of money in finding players who are public favorites but maybe not so beneficial for the teams that they play for. “Look at Dwight Howard. He was a monster but not very good with the Lakers. Kobe Bryant, in my opinion, is nothing but overrated. He’s not super efficient. Now that he’s coming back from an injury, he is not worth very much.”

Sometimes the world misunderstands an entire team that Rynning sees in the proper way—and considering that he can easily make 15 NBA bets in a single day, wagering between $5,000 and $10,000 per bet, those opinions are carefully considered. “Last year I made a lot of money on the Washington Wizards,” he says. “They don’t have a very good coach and started the year 5–27. Then they began playing really good defense, something that often flies under the radar”—and is therefore precisely the sort of thing gamblers should look for when zeroing in on teams to track. “They wound up going on a streak in which they covered 26 out of 28 games, and I got on them early. That’s what I love, finding the underrated nugget, making a lot of money with them, and being correct before anybody else is.” He hesitates for a beat, considers, then adds, “It’s not only about winning tens of thousands of dollars. It’s also about being right. I like the idea that I bought stock in Washington Wizards before other people saw the value. Then the rest of the world caught up.”

For all of Rynning’s astuteness and success, his nerve center is as low-key as his approach to handicapping. He works out of a spare bedroom on the upper floor of his house. The bed remains in place and he has three TVs up on tables in the room. It’s not an enclave with built-in flat-screens and the kind of power-desk that would make an executive envious. But for Rynning, it works just fine. He watches games, gleans information, out-thinks competitors. “Eventually, I’ll have a bunch of TVs up on the wall,” he vows. “But, for now, this setup is perfect.”

As much as Rynning is a laid-back recluse, happy to do his own thing on E.R. Island, Teddy “Covers” Sevransky comes across as more the quintessential sports bettor, the loquacious guy who likes to share opinions, discuss the games, hang in the sports books. Trim and slick looking with a neat beard, he favors the operations run by Cantor Gaming, where he can wager on individual plays and quarters and segments of games. That brings us to Lagasse’s Stadium, Emeril’s pizza and salad and beer joint in Las Vegas’s Palazzo, where Cantor maintains the wagering.

Though Sevransky and Rynning both sell picks via Sportsmemo (an enterprise in which they are co-owners), their gambits for making money through the NBA are completely different. While Rynning takes a bit of a grapeshot approach and has lots of money on lots of games, Sevransky tends to be more surgical, looking for statistical hiccups and riding them until they peter out. “I tend not to be a big picture guy,” he says. “I make money when things happen in the short term that temporarily change the level of play. With that, though, I try to add another level of thinking.

I see a team morphing in a certain direction and maybe that makes a seemingly correct number into the wrong number.”Reaching for an example, he recalls the beleaguered Charlotte Bobcats in 2012. “After having been the worst team in history, they opened last season with a record of 7–7. People assumed that they had improved and become a better team. Not me. I saw the slog coming.” Sevransky recognized that, based on freaky statistics, other bettors and the books would overrate Charlotte in the same way that a frenzy-feeding public can drive up the value of a tech stock that secretly has no legs. “I made money by betting against them for the next 20 games. You pay attention and find these inefficiencies.”

Taking it a step further, there are certain situational quirks—“hidden spots,” as Sevransky calls them—that are worth looking for. For example, while conventional wisdom may hold that a team traveling home from the opposite coast will be a little beaten up if it has to play the next night, Sevransky sees this situation differently. He pays more attention to the team that had a night off after traveling, figuring that it takes a day for the distractions of real life to pile up. “You’ve just gotten back from a road trip and have spent a day dealing with your wife, your kids, your pet, your lawyer,” ticks off Sevransky. “These things arise and they’re distractions.” Also, small picture guy that he is, he looks for minor losing streaks: “A decent NBA team on the road loses two games in a row, you want to bet on them. That is when they dig in their heels”—to win. At least some of the time: “The trick is that it’s team specific. You can’t look at everything league wide.”

Jim Kruger can. In fact, he looks at the league and the year, employing a deep data base to get the largest picture possible and working from there. Formerly a stocks and commodities trader, he applies the Wall Street approach to picking current winners by examining past trends. “It’s amazing, the degree to which history and price-points repeat themselves,” says Kruger, who sells picks via vegassportsauthority.com. “For example, at the start of the season, a team that has already played its first game and is now traveling to play a second game against a team that has not yet begun the season will cover the point spread only 30 percent of the time.” During the season “people think it’s a terrible spot if a team is playing its fourth game in five nights and the books adjust accordingly. I like to know the reality of that situation”—based on what has happened in the past—“and I adjust my numbers accordingly.”

While Bob Voulgaris hired an esteemed scientist from a top East Coast hedge fund to build the computer system that he uses, Kruger makes it sound a lot easier than that. In fact, if you know a bit of coding, he lends the impression that it can be a pretty good DIY project for NBA betting with an edge, though you clearly won’t have a Voulgaris-level edge. You begin by subscribing to a statistical database and then work with a system that allows you to use that information for answering statistical queries: How do you value a decent three-point scoring team vs. an excellent all around shooting team? What is the precise statistical consequence of a team playing its fourth game in five nights? Just how important is the presence of a single player on a particular team?

Kruger advises starting small, developing your techniques while making low-denomination wagers and tightening your handicapping game along the way. Sometimes it’s a matter of knowing when not to bet. Other times it’s waiting for the point spread or money line to fall within your parameters. And all along you need to figure out why you’re right, why you’re wrong, and whether or not you correctly handicapped a losing bet but just happened to get unlucky. “Overall, you need to gamble with a rationale,” he advises. “It needs to be something better than, ‘The Knicks are due.’ ”

Iinterview Erin Rynning just one day before the NBA’s opening night tip-off. All things considered, I can’t help but ask him for a couple of picks. Particularly, I am interested in the one pick that he thinks is a lock for the first night. “There’s no such thing as a lock,” he says, sounding a little bemused. “You can never be 100 percent sure.”

Okay, then, how about his strongest pick?

That one is easy: Play the over on the Clippers vs. the Lakers. “The Clippers have a new head coach, Doc Rivers,” begins Rynning, giving me a good bet and letting me in on his thought process. “They used to be a slow team and Rivers likes to play faster. In the off-season, the Clippers improved offensively but suffered defensively.” So, isn’t that good for the bet?

“Yes, but here’s what bothers me a little bit: They brought in Doc Rivers so that the team could play better defense. On the other hand, Doc got known for being a big defensive guy, but it’s his former assistant who really is a defensive mastermind. Then you have L.A. and they don’t care about defense. Plus they’ve lost two of their good defenders. They’re all offense, totally tempo. They’ll have no resistance against a team with a strong offense.” Now for the (sort of) caveat: “During the early part of the NBA, teams can come out sluggish. For that reason, I don’t like betting overs early in the season. But this was too good to resist.”

I manage to get the bet at over 201, which falls within Rynning’s parameters. I’m getting together with a friend by the name of J.C. and we each wind up wagering $100 on the game. I text my friend Reggie in New York, checking to see if he wants to get in on it. Reggie responds in the negative, telling me he can’t see the score going that high, even after I reveal the source of my information. J.C. and I make our way to the bar of Comme Ça, inside the Cosmopolitan, for cheeseburgers and whiskey cocktails. The food and booze are great, but the game, which plays on a TV at the far end of the bar, is even better. By the start of the fourth quarter, I get a text from Reggie: “Ur bet is a lock. Pace of game is unreal. Ur boy is a genius.” We coast to an easy win, with a nice cushion of points, and a nightcap before heading down to the cage to cash out.

Next day, walking past the Bellagio’s sports book, I can’t help but look at the board inside while recalling Erin Rynning’s answer to my question about who he sees as the underappreciated Washington Wizards of this 2013/2014 NBA season. “The Minnestoa Timberwolves have a chance to be really good,” he responds without hesitation. “A couple of their best players, Ricky Rubio and Kevin Love, didn’t play all the games last season. The T-Wolves have a lot of good players and a good coach. Now they are really hungry and this is it. This is their time. I think they are going to be really good.”I’m not arguing.Michael Kaplan is a Cigar Aficionado contributing editor.